“It was great to walk through the Old City…and just feel the energy!”

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Roger writes lifelaidout to concentrate on helping folks to save time, money and energy by obtaining the best value out of life.

Roger and Jenn in Front of the Louvre, Paris

How and when did you start collecting miles and points?

In 2009, after having a less than pleasant stay at a Westin hotel, I complained to the staff multiple times. I ended up with 40,000 Starwood points for my troubles. That is equivalent to 4 free nights at a Westin or ~$800!

At that point, I started thinking that this “collecting points” thing could be an interesting hobby to pursue.

Why did you start your blog? What’s special about it?

I started thinking about the idea of lifelaidout after having a very frustrating experience finding a NYC apartment 7 years ago.

I found the process extremely complicated. There wasn’t a clear and unbiased guide I could read to figure out how to best go through the process.

So I started thinking about how I could map out some complex life experiences in a simple way for others.

In a nutshell, that’s how my blog lifelaidout was started.

I write about a variety of topics including credit cards, travel, apartments, and personal finance. My main focus is on helping my readers find the best value for their time, money, and energy.

I try to use numbers or create models as much as possible to prove out my thoughts (like I did here to compare the Chase Sapphire Preferred card vs. the Starwood Amex card).

Roger and Jenn in the Old City, Jerusalem

What’s the one single thing people can do to get more miles?

Apply for multiple credit cards when you’re expecting a large purchase. That is how I recently got a bunch of miles.

In the weeks leading up to our wedding, we needed to put down the final payment for our venue. Luckily, I had just read your blog post on how you applied for 16 credit cards in a year (which was amazing!).

I got pretty inspired and decided it would be a good idea to apply for 3 new credit cards.

I split our final wedding payment among those cards to fulfill each card’s minimum spend. This earned me the sign-on bonus for each card in one fell swoop!

That was pretty awesome because I was able to earn a lot of miles quickly! I didn’t have to worry about how to allocate my everyday spend among those cards after that big purchase.

What’s your most memorable travel experience?

I’m going to cheat here and name two, but Cuba and Israel have to be the most memorable travel experiences I’ve had so far.

Americans typically aren’t allowed to visit Cuba legally. I was lucky enough to tag along with my friend’s college for a spring break trip almost 10 years ago. It was such a great experience!

We toured the streets of Havana in a scooter, got to taste the Cuban cigars and rum that I always heard about, and just experience the culture and interacted with locals.

Riding a Scooter Through the Streets of Havana, Cuba

Israel was also an awesome trip for me. It was great to walk through the Old City (in Jerusalem) and just feel the energy.

Millions of people come to the Old City every year. It’s remarkable that such a small stretch of land has been extremely important to so many people for thousands of years.

Aside from the history, Israel also has a lot of great food. We had some of our favorite meals of all time in Israel.

What do your family and friends think of your miles & points hobby?

They’re actually very supportive.

My wife wondered, at first, why we had to put certain types of spend on one card vs. another and if it was really worth the hassle. After staying for “free” at the Sheraton in Tel Aviv and the St. Regis in Rome, she’s been able to see the tangible value of optimizing points.

It’s fun to be able to talk to friends and family about my points hobby. My in-laws, especially, are avid followers of my blog.

At work, I also get a chance to share my hobby with co-workers because I offer free credit card consultations to help them find the right credit card.

Seafood Risotto from Machne Yuda

Is there any tool or trick which you’ve found especially useful in this hobby?

I use AwardWallet to keep track of all of my mileage and point balances.

After I’ve applied for a credit card, I’m pretty diligent about adding an entry into my Google calendar, reminding me when I need to cancel the card to avoid the annual fee.

And lastly, I use the Notepad app on my iPhone to keep track of my gift card balances and expiration dates.

What was the least expected way you’ve earned miles or points?

I was pretty surprised when I got that 40,000 points from the Westin in San Antonio. That was more points than I had ever had before and I was able to utilize it to pay for our hotel in Tel Aviv.

Roger Floating on the Dead Sea

What do you now know about collecting miles and points which you wish you knew when you started out?

I just wish I would have started being a little more deliberate about collecting miles and points before 2009.

Since I started this hobby, I’ve used points to subsidize my international trips to England, France, Italy, and Israel. In my earlier years, I might have taken more trips abroad if I was able to pay for part of the trips with points.

What would your readers be surprised to know about you?

Instead of listening to music, I prefer having a movie playing in the background while I’m blogging. My current rotation of movies is Moneyball, Office Space, 21, and Rounders.

Any parting words?

Collecting miles and points is complicated. There are a lot of variables that can change from year to year, like a hotel program changing their point values or relationship changes between a loyalty program and a credit card – and it totally affects your strategy.

That’s why following a blog like Million Mile Secrets is so valuable because you do a lot of the leg work so others don’t have to.

Roger and Jenn Posing in a Phone Booth in London with Big Ben Nearby

I’d say, focus on optimizing across a couple of loyalty programs and that’s it – try not to overdo it.

Also, don’t be afraid to ask for free miles and points when an airline or hotel has provided you with less than favorable service. That’s how I got the 40,000 points from Starwood – and what got me into this hobby in the first place!

Roger – Thanks for sharing your thoughts on having Big Travel with Small Money!

If you’d like to be considered for our interview series, please send me a note!

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I’ve been to Cuba, too, back in ’99 and directly from Germany.
It was too funny when I got approached literally EVERYWHERE to buy cigars. The craziest was when I was swimming in the ocean and a guy swam up to me and was asking “Do you want cigars?”.
Another one was offering me a box of cigars for one of my rollerblades (1 single boot!!).
We had a great time! 🙂

@dyhppy You can check out the post Anita flagged for the high level summary. For the full detail, basically the Westin at San Antonio overbooked their hotel. As a result, for my first night in San Antonio, they put me up in the Sheraton nearby, but it wasn’t that nice at all. When I went to the Westin the next day to check-in, they said the room wasn’t available yet, so I asked for 10,000 points and they gave it to me. Later that day, at around 3pm, I tried checking in again, and they told me yet again that a room was still NOT available. I asked for another 10,000 points and since it was a different person helping me, they also said they would give it to me. I asked two different people throughout the next two days for 10,000 more points, and they all surprisingly gave me 10,000 points each for a total of 40,000 points.

@Dan, so great that you were able to go to Cuba as well – I had a similar experience of many people on the street asking me if I wanted to buy cigars. However, I never had anyone swim up to me to ask – that is amazing!

If I wanted to visit today…….Would it be worth the hassle? I have a feeling places like Cuba, and North Korea aren’t going to be around in 20 years. (Not that they wont exist, but that they wont be closed off from the world as they are now)

@Jan Given all the mishaps that happened during my stay, I thought it was perfectly acceptable to complain 4 times. The hotel actually was at fault for letting too many people extend their stay, so that’s why they didn’t have a room for me (and others) the first night. They had promised to have a room for me first thing the following morning, but it wouldn’t be until 5pm that day that I’d be able to get into my room. There were some other things they did as well that weren’t so favorable, so all in all, I thought it was more than appropriate to complain 4 times. I certainly didn’t expect to receive 40,000 points, but I’ll take it!

@Rob Good question – while I can’t comment on whether it’s worth the risk, I’m glad I got the opportunity to go. There were certainly tourists from other countries there, but I think the lack of American tourists made the country just a little quieter. It was amazing to see 1950s cars still on the road and cabs that looked like teacups transporting people around. Definitely a unique experience!

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